74148-43-9

Upstream product

• 145603-76-5 Nalanthalide 
• 744261-11-8 (4aR,5S,6S,8aR)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,5,6,7,8,8a-octahhydronaphthalene-2-methanol 
• 744261-14-1 (1R,4aR,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)decahydronaphthalene-1-carbaldehyde 
• 153530-67-7 (4aS,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-5-(4-methylpent-3-enyl)decahydronaphthalen-1-one 
• 91547-51-2 (4aS,5S,8aS)-(+)-3,4,4a,7,8,8a-Hexahydro-5,8a-dimethyl-5-(prop-2-enyl)naphthalene-1,6(2H,5H)-dione 1-(Ethylene Acetal) 
• 890936-27-3 3-[(1R,4aR,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalen-1-yl]hydroxymethyl-5,6-dimethyl-2-methoxy-4H-pyran-4-one 
• 890936-19-3 (4aS,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5-(tert-butyldimethylsiloxypropyl)-5,8a-dimethyl-decahydronaphthalen-1-one 1-ethylene acetal 
• 744261-13-0 (1R,4aR,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalene-1-methanol 
• 890936-22-8 (Z)-(4aS,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-2-hydroxymethylene-5-(4-methylpent-3-enyl)decahydronaphthalen-1-one 
• 890936-25-1 (4aR,5S,6S,8aR)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-5-(4-methylpent-3-enyl)-3,4,4a,5,6,7,8,8a-octahhydronaphthalene-2-carbaldehyde 
• 890936-20-6 (4aS,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-5-(3-hydroxypropyl)decahydronaphthalen-1-one 
• 890936-21-7 (4aS,5S,6S,8aS)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-5-(3-oxopropyl)decahydronaphthalen-1-one 
• 890936-18-2 (4aS,5S,6S,8aS)-5,8a-dimethyl-6-hydroxy-5-(3-hydroxypropyl)decahydronaphthalen-1-one-1-ethylene acetal 
• 744261-18-5 3-[(1R,4aR,5S,6S,8aR)-6-(tert-butyldimethylsiloxy)-5,8a-dimethyl-2-methylene-5-(4-methylpent-3-enyl)-decahydronaphthalen-1-yl]methyl-5,6-dimethyl-2-methoxy-4H-pyran-4-one 

Relevant academic research and scientific papers

Diterpenoid pyrones, novel blockers of the voltage-gated potassium channel Kv1.3 from fungal fermentations

The isolation, structure elucidation and chemical modification of nalanthalide, a novel diterpenoid pyrone blocker of the voltage-gated potassium channel Kv1.3 are reported. The structure-activity relationship of the derivatives with respect to various associated biological activities is also discussed.

Convergent and enantioselective total synthesis of (-)-nalanthalide, a potential Kv1.3 blocking immunosuppressant

The first total synthesis of (-)-nalanthalide (1), a novel blocker of the voltage-gated potassium channel Kv1.3 from a microorganism, was accomplished in a convergent manner by utilizing coupling reaction of the trans-decalin 5 with 3-lithio-γ-pyrone 4. The key intermediate 5 was efficiently prepared from the known trans-decalone 7 through a [2,3]-Wittig rearrangement of the stannylmethyl ether 6 to install the stereogenic center at C9 and the exo-methylene function at C8.

Viridoxins A and B: Novel Toxins from the Fungus Metarhizium flavoviride

The structures of viridoxins A and B, two novel toxins isolated from the mycelial extract of the fungus Metarhizium flavoviride, were established by spectroscopic methods, chemical correlations, and a single-crystal X-ray analysis of viridoxin B.The absolute configuration of the viridoxins was determined by 1H NMR analysis of chiral (R)- and (S)-O-methyl mandelate derivatives of viridoxin A.

Enantioselective total synthesis of novel diterpenoid pyrones (+)-sesquicillin and (-)-nalanthalide from fungal fermentations

We efficiently synthesized (+)-sesquicillin (a glucocorticoid antagonist) and (-)-nalanthalide (a potassium channel Kv1.3 blocker) in a convergent and unified manner starting from (+)-5-methyl-Wieland-Miescher ketone. The synthesis involved the following key steps: (i) a [2,3]-Wittig rearrangement of a stannylmethyl ether to install the stereogenic center at C9 and the exo-methylene functionality at C8 present in the tran/decalin portion, (ii) a coupling reaction of a trans-decalin portion with a γ-pyrone moiety to assemble the requisite whole carbon framework, and (iii) a conversion of a γ-pyrone moiety to an α-pyrone ring to produce (+)-sesquicillin. The present total synthesis has verified the absolute configuration of these natural products.